We introduce phenazine-1,6-dicarboxamides as redox-responsive molecular switches. The reduction of their phenazine core transforms them from hydrogen-bond acceptors into hydrogen-bond donors and thus forces the secondary amide substituents to turn around. The resulting conformational changes are envisioned to form the basis for butterfly coil foldamers undergoing reversible extension and contraction in response to changing their oxidation state.

Nanosized butterfly-coil foldamers containing alternating phenazine-1,6-dicarboxamide and 2,5-dialkoxyterephthalamide moieties have been demonstrated to undergo extension-contraction in response to changing their oxidation state. Both the chemical (catalytic hydrogenation/aerial oxidation) and electrochemical versions of this process have been shown to be clean and fully reversible.

Racemic cyclic hydroxamic acids bearing an aryl substituent adjacent to the hydroxyl group undergo effective acylative kinetic resolution promoted by benzotetramisole (BTM).

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